CA2482131C - Procede semi-synthetique de preparation de n-debenzoylpaclitaxel - Google Patents

Procede semi-synthetique de preparation de n-debenzoylpaclitaxel Download PDF

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Publication number
CA2482131C
CA2482131C CA2482131A CA2482131A CA2482131C CA 2482131 C CA2482131 C CA 2482131C CA 2482131 A CA2482131 A CA 2482131A CA 2482131 A CA2482131 A CA 2482131A CA 2482131 C CA2482131 C CA 2482131C
Authority
CA
Canada
Prior art keywords
formula
compound
nitrobenzenesulfenyl
acid
preparation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
CA2482131A
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English (en)
Other versions
CA2482131A1 (fr
Inventor
Ezio Bombardelli
Gabriele Fontana
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Indena SpA
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Indena SpA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Indena SpA filed Critical Indena SpA
Publication of CA2482131A1 publication Critical patent/CA2482131A1/fr
Application granted granted Critical
Publication of CA2482131C publication Critical patent/CA2482131C/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un procédé de préparation de N-débenzoylpaclitaxel (I) par estérification de la baccatine III protégée en 7 avec un dérivé réactif d'acide carboxylique représenté par la formule générale (II), et par élimination des groupes protecteurs d'ester dans des conditions acides et en une seule étape. Dans la formule (II) R1 représente aryle or hétéroaryle. Le composé représenté par la formule (I) peut être avantageusement utilisé pour la préparation de paclitaxel et analogues.
CA2482131A 2002-04-12 2003-03-24 Procede semi-synthetique de preparation de n-debenzoylpaclitaxel Expired - Lifetime CA2482131C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IT2002MI000782A ITMI20020782A1 (it) 2002-04-12 2002-04-12 Processo semisintetico per la preparazione di n-debenzoilpaclitaxel
ITMI2002A000782 2002-04-12
PCT/EP2003/003017 WO2003087077A1 (fr) 2002-04-12 2003-03-24 Procede semi-synthetique de preparation de n- debenzoylpaclitaxel

Publications (2)

Publication Number Publication Date
CA2482131A1 CA2482131A1 (fr) 2003-10-23
CA2482131C true CA2482131C (fr) 2012-07-17

Family

ID=11449694

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2482131A Expired - Lifetime CA2482131C (fr) 2002-04-12 2003-03-24 Procede semi-synthetique de preparation de n-debenzoylpaclitaxel

Country Status (18)

Country Link
US (1) US7053222B2 (fr)
EP (1) EP1495011B1 (fr)
JP (2) JP5197908B2 (fr)
KR (2) KR20100036394A (fr)
CN (1) CN1310897C (fr)
AT (1) ATE314357T1 (fr)
AU (1) AU2003219094B2 (fr)
CA (1) CA2482131C (fr)
DE (1) DE60303023T2 (fr)
DK (1) DK1495011T3 (fr)
ES (1) ES2254921T3 (fr)
HK (1) HK1075661A1 (fr)
IL (2) IL164486A0 (fr)
IT (1) ITMI20020782A1 (fr)
NO (1) NO328960B1 (fr)
PL (1) PL209650B1 (fr)
RU (1) RU2302415C2 (fr)
WO (1) WO2003087077A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20020782A1 (it) * 2002-04-12 2003-10-13 Indena Spa Processo semisintetico per la preparazione di n-debenzoilpaclitaxel
US7446126B2 (en) 2004-10-08 2008-11-04 Indena S.P.A. Semisynthesis process for the preparation of 10-deacetyl-N-debenzoyl-paclitaxel
ITMI20050614A1 (it) * 2005-04-12 2006-10-13 Indena Spa Processo per la purificazione della 10-deacetilbaccatina iii dalla 10-deacetil-2-debenzoil-2-pentenoilbaccatina iii
WO2008074178A1 (fr) * 2006-11-23 2008-06-26 Shanghai Bailing Pharmaceutical Technology Co., Ltd Nouveau procédé de préparation de paclitaxel semi-synthétique

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ262030A (en) * 1993-02-05 1997-10-24 Bryn Mawr College Process for preparing a taxol intermediate
PL329637A1 (en) * 1996-05-08 1999-04-12 Upjohn Co Taxol obtained method
US5821263A (en) * 1996-08-26 1998-10-13 Bristol-Myers Squibb Company Sulfenamide taxane derivatives
US5917062A (en) * 1997-11-21 1999-06-29 Indena S.P.A Intermediates and methods useful in the semisynthesis of paclitaxel and analogs
ITMI20020782A1 (it) * 2002-04-12 2003-10-13 Indena Spa Processo semisintetico per la preparazione di n-debenzoilpaclitaxel

Also Published As

Publication number Publication date
IL164486A0 (en) 2005-12-18
DE60303023D1 (de) 2006-02-02
KR101159837B1 (ko) 2012-06-25
ES2254921T3 (es) 2006-06-16
WO2003087077A1 (fr) 2003-10-23
HK1075661A1 (en) 2005-12-23
EP1495011B1 (fr) 2005-12-28
RU2004130316A (ru) 2005-06-27
NO20044291L (no) 2004-10-11
KR20100036394A (ko) 2010-04-07
ITMI20020782A0 (it) 2002-04-12
PL371673A1 (en) 2005-06-27
JP2005530729A (ja) 2005-10-13
AU2003219094A1 (en) 2003-10-27
JP2010265274A (ja) 2010-11-25
AU2003219094B2 (en) 2008-06-26
EP1495011A1 (fr) 2005-01-12
ITMI20020782A1 (it) 2003-10-13
NO328960B1 (no) 2010-06-28
PL209650B1 (pl) 2011-09-30
US20050049297A1 (en) 2005-03-03
KR20040105795A (ko) 2004-12-16
CA2482131A1 (fr) 2003-10-23
DE60303023T2 (de) 2006-09-28
US7053222B2 (en) 2006-05-30
CN1646512A (zh) 2005-07-27
ATE314357T1 (de) 2006-01-15
RU2302415C2 (ru) 2007-07-10
CN1310897C (zh) 2007-04-18
IL164486A (en) 2008-11-26
JP5197908B2 (ja) 2013-05-15
DK1495011T3 (da) 2006-05-15

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Effective date: 20230324